The group included more than a dozen young members of the Ice Hockey in Harlem organization and their parents.
O'Ree has run many clinics for Ice Hockey In Harlem since being named the director of youth development for NHL Diversity in 1998.
O'Ree and Simmonds, one of three rookie black players this season in the NHL, autographed team sweaters, T-shirts, sticks, pennants and trading cards for the youngsters and then sat for a question-and-answer session.
The event was part of the NHL's Hockey is for Everyone initiative, a month-long NHL Diversity program that celebrates hockey's growing diversity.
Simmonds also read from "The Autobiography of Willie O'Ree: Hockey's Black Pioneer." Simmonds read the section about O'Ree's call-up to the Boston Bruins on Jan. 18, 1958, to play against the Montreal Canadiens in the Montreal Forum.
"I look back and it feels like yesterday," O'Ree told the children, who ranged from about 10 to 14 years old. "It's a nice feeling to know you have opened doors and broken down barriers, not only for black players, but for all players of color."
O'Ree stressed the value of education, hard work and focus in his remarks.
"The more time you can spend on the ice, the better hockey player you are going to be," said O'Ree, who grew up the youngest of 13 children in one of only two black families in Fredericton, New Brunswick. "I started skating at two years old and I always loved it. I spent all the time I could in winter skating and playing hockey. That's why I was such a good skater."
O'Ree, 74, and Simmonds, 20, both talked about how nervous they were in their first NHL games.
Simmonds made his debut Oct. 11, 2008, in San Jose against the Sharks. Simmonds had no points that night in 12:02 minutes of ice time, but it's a game he'll never forget.
"From the time I stepped on the ice, I had a great, big smile on my face," Simmonds said. "I was kind of overwhelmed on my first shift but then I just settled down. I just love the game, but it took awhile for everything to settle in. My advice is to just give your best effort, all the time, and things can work out well."
Looking at the young faces in the crowd, Simmonds remembered his childhood growing up in neighborhoods in east Toronto, "I remember the first time I went skating, I was three years old. My dad would take me every Saturday. I loved hockey from the time I touched the ice. Dad would build outdoor rinks for us and the other kids in the neighborhood."
Simmonds, O'Ree, and Washington Capitals left winger Donald Brashear conducted a clinic on Feb. 4 at the Fort Dupont Ice Hockey Club, an NHL Diversity partner. The club is the oldest minority youth hockey program in the United States. The Kings were in Washington at that time to play the Capitals.
O'Ree heaped praise on Simmonds for using his personal time on a road trip to help children. He said those kids will remember that day for the rest of their lives.
Simmonds reinforced O'Ree's perspective by saying he had attended the Kevin Weekes' hockey clinic in Toronto when he was 13 and 14. Weekes is also a native of east Toronto and now plays goal for the New Jersey Devils.
"I remember Kevin came out to the camp with Anson Carter, another NHL player, and we were all very excited at meeting two black players who were in the NHL," Simmonds said. "I just want to be able to give back."
"When you make an impact on a boy or a girl, like that, there's no money in the world that can take that away," O'Ree said.
Ezekiel Bennett plays every Saturday and practices every Monday night with Ice Hockey In Harlem in Central Park. He was with his mom, Vilmary, to see O'Ree and Simmonds. He wasn't yet familiar with Simmonds, a rookie, but knew that O'Ree was "the first African-American hockey player." He said he likes Ice Hockey In Harlem "because I get to skate a lot."
Sulayman Ibrahim, 12, asked Simmonds where he'd go if he got traded?
"The Penguins!" he responded and Hradek asked Simmonds if he'd like to play with Sidney Crosby.
"That would be great, but I like playing with the Kings," he said.
O'Ree and Simmonds are 54 years apart and a question from Dylan Garcia, 10, who started skating at 2, further demonstrated the difference in the hockey eras in which they played.
"What kind of stick do you use?" Garcia asked.
"I use a one-piece Bauer composite stick," Simmonds "I've always used them since I was a little kid."
"I used a Northland wooden stick with a flat blade," O'Ree said. "They were a big manufacturer of sticks in my day and if you look at old NHL pictures, you'll see about 90 percent of the players used Northlands. We used to bend the blades a little bit by heating them and then bending them slightly in a door jam."